A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors

Vibhute, Amol M. ; Dhaka, Arun ; Athiyarath, Vignesh ; Sureshan, Kana M. (2016) A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors Chemical Science, 7 (7). pp. 4259-4263. ISSN 2041-6520

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Official URL: http://doi.org/10.1039/C6SC00633G

Related URL: http://dx.doi.org/10.1039/C6SC00633G

Abstract

Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility with substrates having alkenes and the requirement of a stoichiometric amount of promoters, co-promoters and extreme temperatures are some of the limitations. We have developed an efficient methodology for glycosylation via the activation of thioglycoside donors using a catalytic amount of AuCl3 and without any co-promoter. The reaction is very fast, high-yielding and very facile at room temperature. The versatility of this method is evident from the facile glycosylation with both armed and disarmed donors and sterically demanding substrates (acceptors/donors) at ambient conditions, from the stability of the common protecting groups, and from the compatibility of alkene-containing substrates during the reaction.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:119902
Deposited On:18 Jun 2021 07:08
Last Modified:18 Jun 2021 07:08

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